3632+ Vacation Rentals Near Chicago Arts District |
  1. USA
  2. Illinois
  3. Chicago
  4. Chicago Arts District

Travel Some Twosome - Vacation Rentals in Chicago Arts District

3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $264
         

9.6 (27 Reviews)
Apartment
3 BD condo near to downtown, Gold Coast and Michigan Avenue.
  • Air Conditioner
  • Parking
  • TV

View Availability
Mccomick Place/China town getaway From US $338
         

|
New
Apartment
Mccomick Place/China town getaway
  • Parking
  • Pet Friendly
  • Child Friendly

View Availability
The Publishing House B&B From US $206
         

|
9.8 (195 Reviews)
Bed & Breakfast
The Publishing House B&B
  • Air Conditioner
  • TV
  • Wheelchair Accessible

View Availability
52nd Floor MagMile Penthouse Views Fireplace Pool From US $485
         

10.0 (408 Reviews)
Apartment
52nd Floor MagMile Penthouse Views Fireplace Pool
  • Air Conditioner
  • Parking
  • Pool

View Availability
New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
New Luxury 3 Bdr Apt in Chicago C9
  • Air Conditioner
  • Parking
  • Pool

View Availability
HI Chicago Hostel From US $73
         

9.0 (1112 Reviews)
Hostel
HI Chicago Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility

View Availability
51st Floor MagMile Penthouse Views Balcony Pool From US $397
         

10.0 (227 Reviews)
Apartment
51st Floor MagMile Penthouse Views Balcony Pool
  • Air Conditioner
  • Parking
  • Pool

View Availability
Stunning 1 bedroom Apartment with Full Amenities by C9 From US $653
         

|
New
Apartment
Stunning 1 bedroom Apartment with Full Amenities by C9
  • Air Conditioner
  • Parking
  • Pool

View Availability
Mccormick Place Guest House From US $91
         

|
8.8 (46 Reviews)
House
Mccormick Place Guest House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

View Availability
LOCATION! Mins to downtown! Fulton mkt/Noble Square, FREE PARKING & LAUNDRY From US $331
         

9.6 (21 Reviews)
Apartment
LOCATION! Mins to downtown! Fulton mkt/Noble Square, FREE PARKING & LAUNDRY
  • Air Conditioner
  • Parking
  • TV

View Availability
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC From US $296
         

10.0 (330 Reviews)
Apartment
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
  • Air Conditioner
  • Parking
  • TV

View Availability
55th Floor Penthouse with Award-Winning Views From US $1,118
         

10.0 (302 Reviews)
Apartment
55th Floor Penthouse with Award-Winning Views
  • Air Conditioner
  • Parking
  • Pool

View Availability
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place From US $321
         

10.0 (275 Reviews)
Apartment
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
  • Air Conditioner
  • Parking
  • TV

View Availability
53 Floor MagMile Penthouse Views, Balcony, Pool From US $516
         

10.0 (244 Reviews)
Apartment
53 Floor MagMile Penthouse Views, Balcony, Pool
  • Air Conditioner
  • Parking
  • Pool

View Availability
2-Story Penthouse Views, Fireplace, Pool, Gym From US $865
         

10.0 (212 Reviews)
Apartment
2-Story Penthouse Views, Fireplace, Pool, Gym
  • Air Conditioner
  • Parking
  • Pool

View Availability
1F Chicago's Little italy Graystone nearDowntown From US $284
         

10.0 (169 Reviews)
Apartment
1F Chicago's Little italy Graystone nearDowntown
  • Air Conditioner
  • Parking
  • TV

View Availability
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath From US $897
         

10.0 (94 Reviews)
House
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
  • Air Conditioner
  • Parking
  • TV

View Availability
52nd Floor Penthouse with Skyline Views & Pool From US $376
         

10.0 (64 Reviews)
Apartment
52nd Floor Penthouse with Skyline Views & Pool
  • Air Conditioner
  • Parking
  • Pool

View Availability
Spacious 4-Level/4-Bedroom Townhouse in West Loop From US $953
         

10.0 (63 Reviews)
House
Spacious 4-Level/4-Bedroom Townhouse in West Loop
  • Air Conditioner
  • Parking
  • TV

View Availability
Brilliant Downtown Chicago 3-Bedroom Condominium From US $528
         

10.0 (51 Reviews)
Condo
Brilliant Downtown Chicago 3-Bedroom Condominium
  • Air Conditioner
  • TV
  • Balcony/Terrace

View Availability
50th Floor Mag Mile Views, Balcony, Pool, Gym From US $258
         

10.0 (33 Reviews)
Apartment
50th Floor Mag Mile Views, Balcony, Pool, Gym
  • Air Conditioner
  • Parking
  • Pool

View Availability
Prime Location! Modern 3 Bed 3 Bath Rental in Chicago From US $496
         

10.0 (32 Reviews)
Condo
Prime Location! Modern 3 Bed 3 Bath Rental in Chicago
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Spacious & private! Free parking! Great location! From US $197
         

10.0 (31 Reviews)
Apartment
Spacious & private! Free parking! Great location!
  • Air Conditioner
  • Parking
  • TV

View Availability
Gorgeous 3BR River North Condo - Free Parking From US $946
         

10.0 (30 Reviews)
Condo
Gorgeous 3BR River North Condo - Free Parking
  • Air Conditioner
  • TV
  • Security/Safety

View Availability
★ Pro Tip: Travelsometwosome makes it easy to compare the best listings on Travelsometwosome homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Travelsometwosome homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chicago Arts District.

Weather in Chicago Arts District

View the weather forecast for Chicago Arts District before booking your Chicago Arts District Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chicago Arts District, IL

Travelsometwosome offers a large selection of top attractions around Chicago Arts District. Research things to do on your vacation before you visit Chicago Arts District.


Navy Pier Wrigley Field McCormick Place Millennium Park Union Station Soldier Field Willis Tower Art Institute of Chicago United Center Grant Park John G. Shedd Aquarium Chicago Museum of Science and Industry Chicago Theatre Chicago Riverwalk Field Museum of Natural History University of Chicago Brookfield Zoo John Hancock Center Lincoln Park Zoo Water Tower Place

Chicago Arts District Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chicago Arts District?

There are a lot of options in Chicago Arts District. If you plan on staying in the Chicago Arts District area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chicago Arts District:

How many vacation rentals are available in Chicago Arts District?

Currently, the total number of properties listed in 2026 is over 3632 in the Chicago Arts District area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chicago Arts District.